To synthesize a Ugi Product following the EXPLAN005 with benzaldehyde, aniline, 1-pyrenebutyric acid and n-butylisocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 83 in the DEXP014-V2Bfile from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post. The purpose of this experiment is to determine whether this set of starting material is soluble in different solvents. It was determined in Exp181-83 that they are insoluble in methanol.
This experiment is Ranked 83. It is a repeat of Exp 181-83 in three different solvents: ethanol, acetonitrile, and dichloromethane.
Exp186-1 is in ethanol, Exp186-2 is in acetonitrile, and Exp186-3 is in dichloromethane.
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
186-1/83
ethanol
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
186-2/83
acetonitrile
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
186-3/83
dichloromethane
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
Quantity
1000uL
(0.5mmol-50.8uL)
(0.5mmol-45.5uL)
(0.5mmol-144.1mg)
(0.5mmol-53uL)
Density information found on the Ugi Chemicals Page in Left Navigation Bar.
Results
Photos taken directly after all the components were charged and vortexed.
186-1 A
186-2 A
186-3 A
Discussion
Conclusion
The starting materials are insoluble in each solvent.
Log
2008-05-07
16:32- Charged vial 186-1 with 1000 ul of ethanol.
16:36- Charged vial 186-2 with 1000 ul of acetonitrile.
16:40- Charged vial 186-3 with 1000 ul of dichloromethane.
16:44- Weighed out the 1-pyrenebutyric acid for each of the three samples.
16:56- Added the aniline to the vials.
16:59- Vortexed each vial 15 seconds each. Each sample was clear.
17:02- Added the benzaldehyde to each vial.
17:04- Vortexed vials for 2 minutes each. Each sample was clear.
17:12- Added the 1-pyrenebutyric acid to each vial.
17:15- Vortexed each vial 3 min. No clear solution was obtained.
17:25- Added the n-butyl isocyanide to each vial.
17:28- Vortexed 2 minutes each. No clear solutions were obtained.
17:35- Photos were taken of the vials 186-1 A, 186-2 A, and 186-3 A.
Objective
To synthesize a Ugi Product following the EXPLAN005 with benzaldehyde, aniline, 1-pyrenebutyric acid and n-butylisocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.This compounds was ranked 83 in the DEXP014-V2B file from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post. The purpose of this experiment is to determine whether this set of starting material is soluble in different solvents. It was determined in Exp181-83 that they are insoluble in methanol.
Procedure
As described in Explan005This reaction used benzaldehyde, aniline, n-butylisocyanide and 1-pyrenebutyric acid .
This experiment is Ranked 83. It is a repeat of Exp 181-83 in three different solvents: ethanol, acetonitrile, and dichloromethane.
Exp186-1 is in ethanol, Exp186-2 is in acetonitrile, and Exp186-3 is in dichloromethane.
Insoluble
Insoluble
Insoluble
Density information found on the Ugi Chemicals Page in Left Navigation Bar.
Results
Photos taken directly after all the components were charged and vortexed.Discussion
Conclusion
The starting materials are insoluble in each solvent.Log
2008-05-07
16:32- Charged vial 186-1 with 1000 ul of ethanol.16:36- Charged vial 186-2 with 1000 ul of acetonitrile.
16:40- Charged vial 186-3 with 1000 ul of dichloromethane.
16:44- Weighed out the 1-pyrenebutyric acid for each of the three samples.
16:56- Added the aniline to the vials.
16:59- Vortexed each vial 15 seconds each. Each sample was clear.
17:02- Added the benzaldehyde to each vial.
17:04- Vortexed vials for 2 minutes each. Each sample was clear.
17:12- Added the 1-pyrenebutyric acid to each vial.
17:15- Vortexed each vial 3 min. No clear solution was obtained.
17:25- Added the n-butyl isocyanide to each vial.
17:28- Vortexed 2 minutes each. No clear solutions were obtained.
17:35- Photos were taken of the vials 186-1 A, 186-2 A, and 186-3 A.
Tags
benzaldehyde InChI: InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H InChIKey: HUMNYLRZRPPJDN-UHFFFAOYAE
aniline InChI: InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYAP
1-pyrenebutyric acid InChI=1/C20H16O2/c21-18(22)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6H2,(H,21,22) InChIKey: QXYRRCOJHNZVDJ-UHFFFAOYAV
n-butylisocyanide InChI: InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR